α-Methylisotryptamine

Clinical data
Other names	isoAMT; iso-αMT; α-Me-isoT; PAL-569; 1-α-Methyltryptamine; 1-(2-Aminopropyl)indole; 1-API; 1-IT; α-Methyl-isotryptamine
Drug class	Serotonin–norepinephrine releasing agent;Serotonin receptor agonist
Identifiers
IUPAC name 1-indol-1-ylpropan-2-amine
CAS Number	1227465-67-9
PubChemCID	20806570
ChemSpider	19644583
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CN1C=CC2=CC=CC=C21)N
InChI InChI=1S/C11H14N2/c1-9(12)8-13-7-6-10-4-2-3-5-11(10)13/h2-7,9H,8,12H2,1H3 Key:OZPPCCIRSILHOZ-UHFFFAOYSA-N

α-Methylisotryptamine (isoAMT orα-Me-isoT) is a synthetic compound belonging to theisotryptamine family, known for its psychoactive properties. As a structural analog of α-methyltryptamine (αMT), isoAMT exhibitsentactogenic andpsychedelic effects.

α-Methylisotryptamine is amonoamine releasing agent andserotonin receptor agonist of theisotryptamine group.^[1][2][3][4] It is the isotryptaminehomologue ofα-methyltryptamine (αMT), which is a more well-knownserotonergic psychedelic,entactogen, andstimulant of thetryptamine family with similarpharmacologicalactions.^[4][5][6]

Like αMT, α-methylisotryptamine is amonoamine releasing agent.^[1][2] As the (–)-enantiomer, it specifically acts as a preferentialserotonin and norepinephrine releasing agent (SNRA), withEC₅₀Tooltip half-maximal effective concentration values of 177 nM forserotonin release, 81 nM fornorepinephrine release, and 1,062 nM fordopamine release.^[1][2] In contrast toamphetamine and similar agents acting aspotent andselectivedopamine and norepinephrine releasing agents, (–)-α-methylisotryptamine showed nomisuse potential inanimal studies, including nococaine-like effects indrug discrimination tests and no facilitation ofintracranial self-stimulation (ICSS).^[1][2] In addition to its monoamine release, α-methylisotryptamine showsaffinity for serotonin5-HT₂ receptors.^[3]

Aderivative of α-methylisotryptamine,zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-N,N-dimethyl-isoAMT), is a non-hallucinogenic serotonin5-HT_2A receptoragonist and is being developed for potential medical use in the treatmentdepression and otherneuropsychiatric disorders.^{[7][8][9][10][11]} Other derivatives of α-methylisotryptamine have also been developed, such as the selective serotonin5-HT_2C receptor agonists (S)-5,6-difluoro-isoAMT andRo60-0175 ((S)-5-fluoro-6-chloro-isoAMT), among others.^{[12][13][14][15][16]}

• Substituted isotryptamine
• 1ZP2MA
• isoDMT
• 5-MeO-isoDMT
• 6-MeO-isoDMT
• VER-3323
• 1Z2MAP1O
• 3-APBT

• Isotryptamines
• Serotonin-norepinephrine releasing agents
• Serotonin receptor agonists

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